Anodically-coloring electrochromic compounds, and devices and compositions containing same
The present invention relates to an anodically-coloring electrochromic compound represented by the following Formula (I), With reference to Formula (I), R 1 and R 2 are each independently selected from linear or branched C 3 -C 20 alkyl. The present invention also relates to electrochromic devices and compositions that include an anodically-coloring electrochromic compound represented by Formula (I).
1. An electrochromic device comprising:
(a) a first substrate having a surface comprising a first transparent electrode layer;
(b) a second substrate having a surface comprising a second transparent conductive electrode layer,
wherein said first transparent electrode layer and said second transparent electrode layer are in opposing spaced opposition; and
(c) an electrochromic layer interposed between said first transparent electrically conductive electrode layer and said second transparent electrically conductive electrode layer, wherein said electrochromic layer comprises,
(i) a cathodic component,
(ii) an anodic component,
(iii) an electrolyte, and
(iv) a polymer matrix,
wherein said anodic component comprises an anodically-coloring electrochromic compound represented by the following Formula (I),
wherein R 1 and R 2 are each independently selected from linear or branched C 3 -C 20 alkyl.
2. The electrochromic device of claim 1 , wherein R 1 and R 2 are each independently linear or branched C 3 -C 10 alkyl.
3. The electrochromic device of claim 2 , wherein R 1 and R 2 are each independently linear or branched C 4 -C 8 alkyl.
4. The electrochromic device of claim 1 , wherein said cathodic component comprises a 1,1′-disubstituted-4,4′-dipyridinium cation represented by the following Formula (II),
wherein R 3 and R 4 are each independently selected from linear or branched C 1 -C 10 alkyl, unsubstituted aryl, and substituted aryl.
5. The electrochromic device of claim 4 , wherein R 3 and R 4 are each independently selected from linear or branched C 1 -C 4 alkyl, unsubstituted phenyl, and substituted phenyl.
6. The electrochromic device of claim 4 , wherein said cathodic component further comprises counter-anions, wherein each counter-anion of the cathodic component is independently selected from the group consisting of BF 4 − , PF 6 − , ClO 4 − , CF 3 SO 3 − or (CF 3 SO 2 ) 2 N − and (CF 3 SO 2 ) 3 C − .
7. The electrochromic device of claim 1 , wherein said electrolyte comprises,
at least one electrolyte anion, wherein each electrolyte anion is independently selected from bis(perfluoro(linear or branched C 1 -C 6 alkysulfonyl)imide, and
at least one electrolyte cation, wherein each electrolyte cation is independently selected from 1-(linear or branched C 1 -C 6 alkyl)-3-(linear or branched C 1 -C 6 alkyl)imidazolium, or 1-(linear or branched C 1 -C 6 alkyl)-1-(linear or branched C 1 -C 6 alkyl)piperidinium.
8. The electrochromic device of claim 1 , wherein said polymer matrix comprises a polymer, wherein said polymer comprises at least one of poly((meth)acrylonitrile), poly(vinylidene fluoride), poly(vinylidene fluoride-co-perfluoro(linear or branched C 1 -C 6 alkylene)), or poly((linear or branched C 1 -C 8 alkyl)(meth)acrylate).
9. The electrochromic device of claim 1 wherein,
said cathodic component is present in an amount of from 0.8 percent by weight to 6.25 percent by weight,
said anodic component is present in an amount of from 0.8 percent by weight to 6.25 percent by weight,
said electrolyte is present in an amount of from 16.4 percent by weight to 25.0 percent by weight, and
said polymer matrix is present in an amount of from 62.5 percent by weight to 82.0 percent by weight,
the percent weights in each case being based on total weight of said cathodic component, said anodic component, said electrolyte, and said polymer matrix.
10. An electrochromic composition comprising,
(i) a cathodic component,
(ii) an anodic component,
(iii) an electrolyte,
(iv) a polymeric thickener, and
(v) a solvent,
wherein said anodic component comprises an anodically-coloring electrochromic compound represented by the following Formula (I),
wherein R 1 and R 2 are each independently selected from linear or branched C 3 -C 20 alkyl.
11. The electrochromic composition of claim 10 , wherein R 1 and R 2 are each independently C 3 -C 10 alkyl.
12. The electrochromic composition of claim 11 , wherein R 1 and R 2 are each independently linear or branched C 4 -C 8 alkyl.
13. The electrochromic composition of claim 10 , wherein said cathodic component comprises a 1,1′-disubstituted-4,4′-dipyridinium cation represented by the following Formula (II),
wherein R 3 and R 4 are each independently selected from linear or branched C 1 -C 10 alkyl, unsubstituted aryl, and substituted aryl.
14. The electrochromic composition of claim 13 , wherein R 3 and R 4 are each independently selected from linear or branched C 1 -C 4 alkyl, unsubstituted phenyl, and substituted phenyl.
15. The electrochromic composition of claim 13 wherein, said cathodic component further comprises counter-anions, wherein each counter-anion of the cathodic component is selected from the group consisting of BF 4 − , PF 6 − , ClO 4 − , CF 3 SO 3 − or (CF 3 SO 2 ) 2 N − and (CF 3 SO 2 ) 3 C − .
16. The electrochromic composition of claim 10 , wherein said electrolyte comprises,
at least one electrolyte anion, wherein each electrolyte anion is independently selected from bis(perfluoro(linear or branched C 1 -C 6 alkysulfonyl)imide, and
at least one electrolyte cation, wherein each electrolyte cation is independently selected from 1-(linear or branched C 1 -C 6 alkyl)-3-(linear or branched C 1 -C 6 alkyl)imidazolium, or 1-(linear or branched C 1 -C 6 alkyl)-1-(linear or branched C 1 -C 6 alkyl)piperidinium.
17. The electrochromic composition of claim 10 , wherein said polymeric thickener comprises a polymer, wherein said polymer comprises at least one of poly((meth)acrylonitrile), poly(vinylidene fluoride), poly(vinylidene fluoride-co-perfluoro(linear or branched C 1 -C 6 alkylene)), or poly((linear or branched C 1 -C 8 alkyl)(meth)acrylate).
18. The electrochromic composition of claim 10 , wherein said solvent comprises at least one of ethylene carbonate, propylene carbonate, gamma-butyrolactone, gamma-valerolactone, N-methylpyrrolidone, polyethylene glycol, or carboxylic acid esters of polyethylene glycol.
19. The electrochromic composition of claim 10 wherein,
said cathodic component is present in an amount of from 0.2 percent by weight to 3.6 percent by weight,
said anodic component is present in an amount of from 0.2 percent by weight to 3.6 percent by weight,
said electrolyte is present in an amount of from 3.8 percent by weight to 14.3 percent by weight,
said polymeric thickener is present in an amount of from 19.2 percent by weight to 35.7 percent by weight, and
said solvent is present in an amount of from 42.8 percent by weight to 76.6 percent by weight,
the percent weights in each case being based on total weight of said cathodic component, said anodic component, said electrolyte, said polymeric thickener, and said solvent.